15-Crown-5 Property

Melting point:

-20°C(lit.)

Boiling point:

93-96 °C/0.05 mmHg (lit.)

Density 

1.113 g/mL at 20 °C (lit.)

vapor pressure 

0.5-0.82Pa at 20-25℃

refractive index 

n20/D 1.465(lit.)

Flash point:

>230 °F

storage temp. 

room temp

solubility 

Miscible with organic solvents.

form 

Liquid

color 

Clear colorless to light yellow

Specific Gravity

1.109

Water Solubility 

MISCIBLE

Sensitive 

Hygroscopic

BRN 

1618144

Stability:

Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air.

LogP

-0.9 at 20℃ and pH7.7

Surface tension

68.5mN/m at 1g/L and 20℃

CAS DataBase Reference

33100-27-5(CAS DataBase Reference)

NIST Chemistry Reference

15-Crown-5(33100-27-5)

EPA Substance Registry System

1,4,7,10,13-Pentaoxacyclopentadecane (33100-27-5)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/38-36-20/22-36/37/38-20/21/22

Safety Statements 

26-39-36

RIDADR 

2810

WGK Germany 

3

RTECS 

SB0200000

F 

10-21

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29329995

Toxicity

LD50 orl-rat: 1410 mg/kg DCTODJ 1,339,78

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

15-Crown-5 Chemical Properties,Usage,Production

use

15-crown-5 has also been used to isolate salts of oxonium ions. For example, from a solution of tetrachloroauric acid, the oxonium ion [H7O3]+ has been isolated as the salt [(H7O3)(15-crown-5)2][AuCl4].

Introduction

The single nitrogen-containing derivative of 15-crown-5 is called aza-15-crown-5; the prefix “mono” is unnecessary. When two or more nitrogen atoms are present, the standard prefixes di-, tri-, etc. are applied. The term “monoazacrowns” is used here to designate the class of macrocycles containing a single nitrogen in combination with oxygen atoms as the macrocyclic donor array.

Chemical Properties

colourless liquid

Uses

15-Crown-5 is used as an efficient phase transfer catalyst and as a complexing agent. It is used to isolate oxonium ion (H7O3)+ salts especially from a solution of tetrchloroauric acid. It catalyzes the O-alkylation of the sodium salts of carboxylic acids in the penicillin and cephalosporin series, thereby facilitating esterification reaction without usage of acid. It is also used to facilitate the Williamson synthesis of ethers with hindered alcohols and sodium hydride. It is used with lithium aluminum hydride, for performing reduction reactions in hydrocarbon solvents. Further, it is involved in the Horner-Wadsworth-Emmons reaction to prepare stilbenes from aldehydes.

Definition

ChEBI: A saturated organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether.

General Description

15-Crown-5 is a crown ether generally used as a ligand in coordination chemistry because of its strong chelating property with certain alkali cations to form complexes. Some derivatives of 15-crown-5 are used as sensors and probes in different physical-chemical processes, phase-transfer reactions, and selective capture of ions for separation and transport.

Safety Profile

Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye . When heated to decomposition it emits acrid smoke and irritating fumes

Purification Methods

Dry it over 3A molecular sieves and distil it in a high vacuum. [Beilstein 19/12 V 252.]